Sulfamic Acid → HCID 70463777, compound

HRID 1902935Notes

Reaction equation

HRID 1902935 reaction equation
NS(O)(=O)=O.ClCCl.[CH3:9][Si:10]([CH3:22])([CH3:21])NS(C1C=CC=CC=1)(=O)=O.[CH3:23][C:24]1[CH2:25][S:26](=[O:46])[C@@H:27]2[CH:34]([NH:35][C:36](=[O:44])[CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:33](=[O:45])[N:28]2[C:29]=1[C:30]([OH:32])=[O:31].[Br:47]N1C(=O)CCC1=O>>[Br:47][CH2:23][C:24]1[CH2:25][S:26](=[O:46])[C@@H:27]2[CH:34]([NH:35][C:36](=[O:44])[CH2:37][C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:33](=[O:45])[N:28]2[C:29]=1[C:30]([O:32][Si:10]([CH3:22])([CH3:21])[CH3:9])=[O:31]

Participants

6

Reactant 5

HCID 5987Sulfamic AcidHCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 12271451N-(Trimethylsilyl)benzenesulfonamideHCID 70485748HCID 70485748, compound

Product 1

HCID 70463777HCID 70463777, compoundYield 40%

Procedure

0.1 mg (1 mmole) of amidosulfonic acid was added to the clear solution obtained by refluxing 75 ml of dichloromethane containing 0.76 g (3.3 mmoles) of N-trimethylsilylbenzenesulfonamide and 350 mg (1.0 mmole) of 3-methyl-7-phenylacetamido-3-cephem-4-carboxylic acid-1-oxide for one and a half hours and the mixture obtained was cooled in an ice-bath. Bromination was carried out in one hour with 0.26 g (1.46 mmoles) of N-bromosuccinimide as the brominating agent to obtain a 40% yield of trimethylsilyl 3-bromomethyl-7-phenylacetamido-3-cephem-4-carboxylate-1-oxide.

Workup

  1. customobtained
  2. customthe mixture obtained
  3. temperaturewas cooled in an ice-bath

Sources & evidence

ORD record
ord-25a9e41cc9354ebd8dd61a0c521f4611
Source dataset
uspto-grants-1982_12
Patent number
US04366315

Reaction notes

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